Synthesis of metallocomplexes of water soluble bisquinolinylporhyrins as potential antimicrobial agents

Yu. V. Ishkov, S. V. Vodzinskii, M. B. Galkin, L. G. Kladko, O. V. Mazepa

Анотація


At present, extensive research is being carried out on the phenomenon of resistance of microbes to antibiotics, including the newest of them. Among the most promising drug candidates for treatment such superbugs is derivatives of 5,15-disubstituted water-soluble porphyrins developed and patented by Destiny Pharma, UK. Here, we continued of our investigation of quinolinylporphyrins and report about synthesis of 5,15-di(n-propyl)-10,20-di(3-quinolinyl)porphyrine and its isomer - 5,10-di(n-propyl)-15,20-di(3-quinolinyl)porphyrine and their complexes with Fe and Mn. The porphyrins was obtained by mixed aldehydes condensation of mixture quinoline-3-carbaldehyde and n-butyraldehyde with pyrrole in propionic acid with small amount propionic anhydride. Above mentioned porphyrins was separated and purified by column chromatography on silica gel and their Fe and Mn complexes was synthesized in refluxing DMF by treatment respectively FeCl3 and Mn(CH3CO2)2. Water-soluble form of the metalloporphyrines was obtained by quaternization of nitrogen atom of quinolinyl substituents by methyl-paratoluenesulfonate for further investigation their antimicrobial properties.


Посилання


Farrell D.J., Robbins M., Rhys-Williams W., Love W.G. Investigation of the Potential for Mutational Resistance to XF-73, Retapamulin, Mupirocin, Fusidic Acid, Daptomycin, and Vancomycin in Methicillin-Resistant Staphylococcus aureus Isolates during a 55-Passage Study. Antimicrob. Agents Chemoter. 2011. vol. 55, no 3, pp. 1177-1181. http://dx.doi.org/10.1128/AAC.01285-10Love

W.G., Rhys-Williams W., Brundish D. Uses of porphyrin compounds. US Patent 7977474 B2. Int. Cl. C07D 487/22, A61K 31/40, 31/44, A61B 5/055. publ. 12.07.2011.

3. www.destinypharma.com

Vodzinskii S.V., Kladko L.G., Mazepa A.V., Galkin B.N., Ishkov Yu.V. Sintez dikhinolinilporfirinov kak potencialnikh antibakterialnikh agentov. Ukrainskij khimicheskij zhurnal. 2016, vol. 82, no 6, pp. 118-122. (in Ukrainian)

Bogatskii A.V., Zhilina Z.I., Vodzinskii S.V., Zakharova R.M. Porfiriny i ih proizvodnye. VI. Sintez i svoistva poverkhnostno-aktivnykh mezo-zameschshenykh porfirinov. Russ. J. Org. Chem., 1989, vol. 21, no 3, pp. 649-654. (in Russian).

Zymalkowski F., Tinapp P. Zur Chemie des Chinolin-carbaldehyds-(3). Justus Liebigs Ann. Chem., 1966, vol. 699, pp. 98-106. http://dx.doi.org/10.1002/jlac.19666990110

Adler A.D., Longo F.R., Kampas F., Kim J. On the preparation of metalloporphyrins. J. Inorg. Nucl. Chem, 1970, vol. 32, no 7, pp. 2443-2445. https://doi.org/10.1016/0022-1902(70)80535-8

Vodzinskii S.V., Zhilina Z.I., Andronati S.A. Patent USSR 1541211. Sposob poluchenija tetratozil'noj soli meso-tetrakis-(N-methyl-4-pyridyl)porfirina. 1990. (in Russian)


Пристатейна бібліографія ГОСТ


1. Farrell D.J., Robbins M., Rhys-Williams W., Love W.G. Investigation of the Potential for Mutational Resistance to XF-73, Retapamulin, Mupirocin, Fusidic Acid, Daptomycin, and Vancomycin in Methicillin-Resistant Staphylococcus aureus Isolates during a 55-Passage Study. Antimicrob. Agents Chemoter. 2011. vol. 55, no 3, pp. 1177-1181. http://dx.doi.org/10.1128/AAC.01285-10Love

2. W.G., Rhys-Williams W., Brundish D. Uses of porphyrin compounds. US Patent 7977474 B2. Int. Cl. C07D 487/22, A61K 31/40, 31/44, A61B 5/055. publ. 12.07.2011.

3. www.destinypharma.com

4. Vodzinskii S.V., Kladko L.G., Mazepa A.V., Galkin B.N., Ishkov Yu.V. Sintez dikhinolinilporfirinov kak potencialnikh antibakterialnikh agentov. Ukrainskij khimicheskij zhurnal.  2016, vol. 82, no 6, pp. 118-122. (in Ukrainian)

5. Bogatskii A.V., Zhilina Z.I., Vodzinskii S.V., Zakharova R.M. Porfiriny i ih proizvodnye. VI. Sintez i svoistva poverkhnostno-aktivnykh mezo-zameschshenykh porfirinov. Russ. J. Org. Chem., 1989, vol. 21, no 3, pp. 649-654. (in Russian).

6. Zymalkowski F., Tinapp P. Zur Chemie des Chinolin-carbaldehyds-(3). Justus Liebigs Ann. Chem., 1966, vol. 699, pp. 98-106. http://dx.doi.org/10.1002/jlac.19666990110

7. Adler A.D., Longo F.R., Kampas F., Kim J. On the preparation of metalloporphyrins. J. Inorg. Nucl. Chem, 1970, vol. 32, no 7, pp. 2443-2445. https://doi.org/10.1016/0022-1902(70)80535-8

8. Vodzinskii S.V., Zhilina Z.I., Andronati S.A. Patent USSR 1541211. Sposob poluchenija tetratozil'noj soli meso-tetrakis-(N-methyl-4-pyridyl)porfirina. 1990. (in Russian)





DOI: https://doi.org/10.18524/2304-0947.2017.4(64).118239

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